4084-27-9 Usage
Description
3-Deoxyglucosone, also known as 3-DG, is a highly reactive 2-oxoaldehyde intermediate of the Maillard reaction produced during oxidative stress in response to excess sugar consumption and in association with diabetes. It is a precursor for the formation of advanced glycation end products and because it readily reacts with protein amino groups, it is also used for crosslinking studies. 3-Deoxyglucosone is an amorphous yellow solid and can be used as a reference for the analysis and detection of glucose degradation products and glycating agents.
Uses
Used in Chemical Research:
3-Deoxyglucosone is used as an intermediate in the Maillard reaction for the study of protein-glucose interactions and the formation of advanced glycation end products. This application is crucial for understanding the role of 3-DG in various pathological effects, such as carcinogenesis.
Used in Analytical Chemistry:
3-Deoxyglucosone is used as a reference compound for the analysis and detection of glucose degradation products and glycating agents. This application is essential for monitoring and controlling the quality of products in the food and pharmaceutical industries.
Used in Crosslinking Studies:
3-Deoxyglucosone is used as a crosslinking agent in the study of protein-protein interactions, as it readily reacts with protein amino groups. This application is valuable for understanding the structural and functional aspects of proteins and their interactions in biological systems.
Used in Medical Research:
3-Deoxyglucosone is used as a model compound to study the effects of diabetes and oxidative stress on the human body. This application is important for developing therapeutic strategies to combat the complications associated with diabetes and other related conditions.
Used in Pharmaceutical Industry:
3-Deoxyglucosone is used as a starting material for the synthesis of various pharmaceutical compounds. This application is significant for the development of new drugs targeting diabetes and its associated complications.
Check Digit Verification of cas no
The CAS Registry Mumber 4084-27-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,8 and 4 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4084-27:
(6*4)+(5*0)+(4*8)+(3*4)+(2*2)+(1*7)=79
79 % 10 = 9
So 4084-27-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1
4084-27-9Relevant articles and documents
Formation of Reactive Intermediates, Color, and Antioxidant Activity in the Maillard Reaction of Maltose in Comparison to d -Glucose
Kanzler, Clemens,Schestkowa, Helena,Haase, Paul T.,Kroh, Lothar W.
, p. 8957 - 8965 (2017/10/17)
In this study, the Maillard reaction of maltose and d-glucose in the presence of l-alanine was investigated in aqueous solution at 130 °C and pH 5. The reactivity of both carbohydrates was compared in regards of their degradation, browning, and antioxidant activity. In order to identify relevant differences in the reaction pathways, the concentrations of selected intermediates such as 1,2-dicarbonyl compounds, furans, furanones, and pyranones were determined. It was found, that the degradation of maltose predominantly yields 1,2-dicarbonyls that still carry a glucosyl moiety and thus subsequent reactions to HMF, furfural, and 2-acetylfuran are favored due to the elimination of d-glucose, which is an excellent leaving group in aqueous solution. Consequently, higher amounts of these heterocycles are formed from maltose. 3-deoxyglucosone and 3-deoxygalactosone represent the only relevant C6-1,2-dicarbonyls in maltose incubations and are produced in nearly equimolar amounts during the first 60 min of heating as byproducts of the HMF formation.
Identification and determination of α-dicarbonyl compounds formed in the degradation of sugars
Usui, Teruyuki,Yanagisawa, Satoshi,Ohguchi, Mio,Yoshino, Miku,Kawabata, Risa,Kishimoto, Junko,Arai, Yumi,Aida, Kaoru,Watanabe, Hirohito,Hayase, Fumitaka
, p. 2465 - 2472 (2008/03/27)
The α-dicarbonyl compounds formed in the degradation of glucose and fructose were analyzed by HPLC using 2,3-diaminonaphthalene as derivatizing reagent, and identified as glucosone (GLUCO), 3-deoxyglucosone (3DG), 3-deoxyxylosone (3DX), tetrosone (TSO), triosone (TRIO), 3-deoxytetrosone (3DT), glyoxal (GO), and methylglyoxal (MGO). The results suggest that α-dicarbonyl compounds were formed from glucose via non-oxidative 3-deoxyglucosone formation and oxidative glucosone formation in glucose degradation. In addition, TRIO, GO, and MGO were also formed from glyceraldehyde as intermediate. The α-dicarbonyl compounds might be formed from glucose via these pathways in diabetes.
